N-Benzylnormechlorethamine → 4-Piperidinecarbonitrile, 4-phenyl-1-(phenylmethyl)-, hydrochloride (1:1)

HRID 1253367Notes

Reaction equation

HRID 1253367 reaction equation
[Cl:1][CH2:2][CH2:3][N:4]([CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH2:5][CH2:6]Cl.[C:15]1([CH2:21][C:22]#[N:23])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[OH-].[Na+]>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1>[ClH:1].[CH2:8]([N:4]1[CH2:5][CH2:6][C:21]([C:22]#[N:23])([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:2][CH2:3]1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

6

Reactant 3

HCID 5928N-BenzylnormechlorethamineHCID 8794PhenylacetonitrileHCID 14798Sodium Hydroxide2×

Product 1

HCID 126520624-Piperidinecarbonitrile, 4-phenyl-1-(phenylmethyl)-, hydrochloride (1:1)Yield 70%

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 1140TolueneSolvent

Conditions

Temperature
85 °C

Procedure

In another run following the procedure described in Example 3 using 151.2 g of toluene solution containing 78.5 g of N,N-bis(2-chloroethyl)benzylamine, 39.8 g of phenylacetonitrile, 109 g of 50% aqueous sodium hydroxide solution, 11.6 g of tetra-n-butylammonium hydrogen sulfate, adding the sodium hydroxide solution over a period of twenty minutes and heating the reaction mixture at 85° C. for four hours, there was obtained 74.1 g (70% yield based on N,N-bis(2-chloroethyl)benzylamine) of 1-benzyl-4-cyano-4-phenylpiperidine hydrochloride, m.p. 261°-263° C.

Sources & evidence

ORD record
ord-86262d54711245adb75cc558ee87afd0
Source dataset
uspto-grants-1988_05
Patent number
US04748276

Reaction notes

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